Vacation rentals with a pool in Hillcrest, San Diego

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Hillcrest, San Diego

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in San Diego

4.97 out of 5 average rating, 340 reviews

Groovy canyon studio pool & spa blocks from SDSU

It’s a groovy studio splashed with color :) Enjoy this slice of paradise hosted by Airbnb super hosts. You can splendor in their thrifty take on the San Diego stay. Bask in the blissful views, and spoil yourself in the spa! If it gets too hot, hop in the pool! No worries allowed at this groovy getaway. We have unique booking methods! Short term stays less than 28 days are available for booking 1 month in advance. If it's over a month before your visit, our calendar only allows longterm booking

May 23 – 30

$144 per night

Guest favorite

Home in San Diego

4.97 out of 5 average rating, 118 reviews

Luxe Home - Heated Pool - Steps to Best Dining

In the heart of North Park, have it all, location, privacy & space, w/ this sophisticated & completely remodeled 1914 craftsman style home. Featuring a stunning outdoor paradise w/ a brand new 30 ft. Trex deck, heated pool/hot tub, resort lounge furniture, 65-inch outdoor tv, market lights & 6-burner gas grill. An open concept, 4 bed, 2.5 bath home is a true hidden gem - including a dreamy chef’s kitchen, stunning Carrera marble bathrooms, original hardwood floors & coffered boxed beam ceilings.

Nov 30 – Dec 7

$679 per night

Superhost

Guesthouse in San Diego

4.91 out of 5 average rating, 247 reviews

Green Door Cottage

Enjoy our new, fully renovated (2021) tiny Cottage which holds a timeless charm and is also filled with a modern touch. Close to all the wonderful things San Diego has to offer - beaches, downtown, the zoo, Padres games, SeaWorld, SAN airport, Old Town, SDSU, you name it! Nice sized turf yard with total privacy and an amazing back deck! Outside table and fire pit are perfect for the cool nights of San Diego. If you need more space, check out our other listing, Pink Door Craftsman (sleeps 7)!

Sep 22 – 29

$119 per night

Guest favorite

Guesthouse in Coronado

4.85 out of 5 average rating, 270 reviews

Coronado Island Pool Cottage

2 blocks from the beach, the Cottage offers a private, clean & quiet stay with your exclusive use of the pool, jacuzzi, bikes, beach items, surfboards, deck chairs, Cable TV & Wifi all included. 3 rooms: QUEEN BEDROOM has AC, heater, ironing, hangers & 8 foot mirrors. LOUNGE ROOM has AC, heater, queen sofa-bed, Cable TV, microwave, fridge, toaster, coffee/tea & bottled water. BATHROOM has walk-in shower, ALL toiletries & towels. BEFORE BOOKING, please click & read the “SHOW MORE" details here:

Nov 11 – 18

$134 per night

Guest favorite

Guesthouse in San Diego

4.93 out of 5 average rating, 122 reviews

Modern Guest House with pool, steps to SDSU

Casita within easy walking distance to SDSU, Viejas Arena, Cal Coast Credit Union Open Air Theatre, shops, and transit. Casita includes Tempur-Pedic Queen bed and a love seat which converts to twin bed. Enjoy the peaceful canyon side garden, firetpit and pool, or relax in the hammock. Panoramic door opens completely to let in our wonderful weather and the view. Note: Pool is heated with a solar cover, comfy for swimming APR-OCT. Max 3 guests, no children/infants due to unfenced pool.

Sep 5 – 12

$104 per night

Guest favorite

Home in San Diego

4.95 out of 5 average rating, 174 reviews

Casa Paradiso: Pool, Hot Tub, Outdoor Lounge!

Why stay at an ordinary vacation rental when you could make memories somewhere EXTRA-ordinary? When you and your crew pull up to Casa Paradiso, typical expressions might include “Whoa!”, “OMG!”, and “Can you believe this place?!” Casa Paradiso by Rental With A View in San Diego is a one-of-a kind luxury resort home located in the ♥ of the city! If you know San Diego, you know Mission Hills is the best place to be, offering both privacy and proximity to all major attractions and beaches.

Nov 29 – Dec 6

$897 per night

Guest favorite

Guesthouse in Mission Hills

4.94 out of 5 average rating, 118 reviews

Central Guesthouse w/ Private Pool & Full Kitchen

Perfect poolside retreat suitable for small families and couples! This suite boasts a fully-equipped kitchen, a private pool, front patio and sunbathing deck! You'll enjoy a luxurious king-size bed and a convenient full-size fold-out option, accompanied by many amenities necessary for a memorable stay. Located in one of San Diego's most central neighborhoods of Mission Hills, you're just a stroll away from restaurants, cocktail bars, the light rail, and easy access to the I-5 highway.

Sep 25 – Oct 2

$251 per night

Guest favorite

Home in San Diego

4.98 out of 5 average rating, 240 reviews

Resort Style Living with Pool, Spa, and Bay Views!

Resort style home with a solar heated pool, hot tub, outdoor entertaining space, bay and ocean views, multiple patios, modern amenities, comfortable beds, and more. Convenient location to freeways, Seaworld, Mission Bay, Beaches, Downtown, Balboa Park, Airport, La Jolla and other attractions. Perfect for families and groups. Two car garage parking included. 2300 square feet of indoor living and much more outdoors. Your ideal home base for enjoying all that San Diego has to offer.

Oct 16 – 23

$726 per night

Guest favorite

Condo in San Diego

4.99 out of 5 average rating, 107 reviews

Luxury Oceanfront Condo with Unbelievable Views

Welcome to your Oasis! You will be completely in awe of the breathtaking views that Sunset Pacifica has to offer. This fully renovated condo features two ensuite bedrooms decorated with the beachy SoCal vibe you are looking for. Centrally located on the boardwalk and just minutes to La Jolla, Downtown, the famous SD Zoo, Embarcadero, restaurants, bars and entertainment. There is so much to do here or just lounge around poolside or on the sandy shores of the beautiful Pacific Ocean.

Sep 21 – 28

$629 per night

Guest favorite

Guesthouse in Mission Hills

4.91 out of 5 average rating, 414 reviews

Mission Hills Charming suite, walkable to all.

Heart of Mission Hills, upscale area, this private guest suite, separate from the house, is perched above the pool (separate building from main house), own entrance; sure to provide privacy. We are minutes from airport, walking distance to coffee & restaurants and central to all of SD. Please note this property is wiped down after each visit with Clorox as well as all linens washed. We also don’t rent back to back giving time for thorough cleaning.

Sep 3 – 10

$85 per night

Guest favorite

Home in Mission Hills

4.94 out of 5 average rating, 203 reviews

Boutique home with view, heated pool, spa + cabana

Heated pool, spa, cabana and view. Boutique hotel vibes in San Diego. Palm Springs meets South Beach with a splash of groovy. Location is perfect for Downtown, conventions, shows in town. Highway friendly. Private backyard for bbq, food, drinks and relaxing. Pool is heated with cozy spa to relax and watch the planes take off. Hi speed Wifi, smart TV's, HBO, NFL Package, record player with albums. 19 speakers in the ceilings with audio hub plug in.

Nov 22 – 29

$525 per night

Guest favorite

Guesthouse in San Diego

4.94 out of 5 average rating, 333 reviews

The BEST NEST Clean, peaceful, private, affordable

This lovely private & separate unit is comfortable, clean and convenient. Your completely private suite is accessible via your own entrance. Minutes from major attractions, away from the hustle and bustle. Full kitchen for easy meal preparation. Located in a nice usually quiet neighborhood, close to major freeways. Enjoy the gorgeous San Diego weather in the quaint outdoor patio area.

Feb 8 – 15

$96 per night